NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	573.2
Volume:	569.161
LogP:	4.83
LogD:	3.156
LogS:	-6.331
# Rotatable Bonds:	8
TPSA:	106.84
# H-Bond Aceptor:	10
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.223
Synthetic Accessibility Score:	3.227
Fsp3:	0.281
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.479
MDCK Permeability:	5.5132160923676565e-05
Pgp-inhibitor:	0.987
Pgp-substrate:	0.347
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.062

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	81.90393829345703%
Volume Distribution (VD):	0.673
Pgp-substrate:	8.466703414916992%

ADMET: Metabolism

CYP1A2-inhibitor:	0.092
CYP1A2-substrate:	0.974
CYP2C19-inhibitor:	0.631
CYP2C19-substrate:	0.592
CYP2C9-inhibitor:	0.669
CYP2C9-substrate:	0.942
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.95
CYP3A4-inhibitor:	0.302
CYP3A4-substrate:	0.859

ADMET: Excretion

Clearance (CL):	7.866
Half-life (T1/2):	0.471

ADMET: Toxicity

hERG Blockers:	0.075
Human Hepatotoxicity (H-HT):	0.089
Drug-inuced Liver Injury (DILI):	0.912
AMES Toxicity:	0.314
Rat Oral Acute Toxicity:	0.219
Maximum Recommended Daily Dose:	0.866
Skin Sensitization:	0.027
Carcinogencity:	0.032
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.667

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC476995

Natural Product ID:	NPC476995
*Common Name:**	Lamellarin gamma acetate
IUPAC Name:	[12-(3,5-dimethoxyphenyl)-18-hydroxy-8,16,17-trimethoxy-4-oxa-1-azapentacyclo[11.8.0.02,11.05,10.014,19]henicosa-2(11),5,7,9,12,14,16,18-octaen-7-yl] acetate
Synonyms:	Lamellarin Gamma Acetate
Standard InCHIKey:	VJXXWWWYRUHHOU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C32H31NO9/c1-16(34)42-26-14-24-22(13-25(26)38-4)29-23(15-41-24)33-8-7-20-21(12-27(39-5)32(40-6)31(20)35)30(33)28(29)17-9-18(36-2)11-19(10-17)37-3/h9-14,35H,7-8,15H2,1-6H3
SMILES:	CC(=O)OC1=C(C=C2C(=C1)OCC3=C2C(=C4N3CCC5=C(C(=C(C=C54)OC)OC)O)C6=CC(=CC(=C6)OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44559518
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000090] Pyrroles [CHEMONTID:0002257] Substituted pyrroles [CHEMONTID:0002334] Phenylpyrroles

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO16570	Didemnum obscurum	Species	Didemnidae	Eukaryota	n.a.	Tiruchandur coast in the Gulf of Mannar, Tamilnadu, India	2002-FEB	PMID[15270574]
NPO16570	Didemnum obscurum	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2
Others	5

Activity Type	# Activity
Others	7

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity	Activity	=	0	%	PMID[15270574]
NPT1	Others	Radical scavenging activity	Activity	=	21.68	%	PMID[15270574]
NPT1	Others	Radical scavenging activity	Activity	=	43.36	%	PMID[15270574]
NPT1	Others	Radical scavenging activity	Activity	=	65.04	%	PMID[15270574]
NPT1	Others	Radical scavenging activity	IC50	=	86720000	nM	PMID[15270574]
NPT1	Others	Radical scavenging activity	IC50	=	5630000	nM	PMID[15270574]
NPT2	Others	Unspecified	Ratio IC50	=	0.01	n.a.	PMID[15270574]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC476995 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	405
0.1-0.2	2117
0.2-0.3	9583
0.3-0.4	7991
0.4-0.5	7957
0.5-0.6	11837
0.6-0.7	2553
0.7-0.8	240
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9665	High Similarity	NPC476994
0.9619	High Similarity	NPC476996
0.9619	High Similarity	NPC476998
0.9573	High Similarity	NPC476999
0.9571	High Similarity	NPC476997
0.8831	High Similarity	NPC129897
0.8426	Intermediate Similarity	NPC318068
0.8363	Intermediate Similarity	NPC255800
0.8363	Intermediate Similarity	NPC96584
0.8356	Intermediate Similarity	NPC201508
0.8108	Intermediate Similarity	NPC473822
0.7991	Intermediate Similarity	NPC148409
0.7965	Intermediate Similarity	NPC122463
0.7964	Intermediate Similarity	NPC112206
0.7964	Intermediate Similarity	NPC202605
0.7956	Intermediate Similarity	NPC174049
0.7928	Intermediate Similarity	NPC474594
0.7839	Intermediate Similarity	NPC49672
0.7815	Intermediate Similarity	NPC284141
0.7808	Intermediate Similarity	NPC164374
0.7808	Intermediate Similarity	NPC137929
0.7764	Intermediate Similarity	NPC217554
0.7763	Intermediate Similarity	NPC469440
0.7738	Intermediate Similarity	NPC474595
0.7723	Intermediate Similarity	NPC203168
0.7713	Intermediate Similarity	NPC290689
0.7713	Intermediate Similarity	NPC219664
0.7706	Intermediate Similarity	NPC200888
0.7682	Intermediate Similarity	NPC469792
0.7679	Intermediate Similarity	NPC11408
0.7671	Intermediate Similarity	NPC31930
0.7664	Intermediate Similarity	NPC469390
0.7661	Intermediate Similarity	NPC4071
0.7661	Intermediate Similarity	NPC476582
0.7661	Intermediate Similarity	NPC476578
0.7658	Intermediate Similarity	NPC313189
0.7652	Intermediate Similarity	NPC118121
0.7647	Intermediate Similarity	NPC36229
0.7647	Intermediate Similarity	NPC16452
0.7647	Intermediate Similarity	NPC476581
0.7644	Intermediate Similarity	NPC53069
0.7644	Intermediate Similarity	NPC296482
0.7644	Intermediate Similarity	NPC202768
0.7639	Intermediate Similarity	NPC85381
0.7632	Intermediate Similarity	NPC204446
0.7611	Intermediate Similarity	NPC284685
0.7581	Intermediate Similarity	NPC191489
0.7557	Intermediate Similarity	NPC66815
0.7546	Intermediate Similarity	NPC41122
0.7546	Intermediate Similarity	NPC318805
0.7534	Intermediate Similarity	NPC304183
0.75	Intermediate Similarity	NPC135549
0.749	Intermediate Similarity	NPC107123
0.749	Intermediate Similarity	NPC473183
0.7489	Intermediate Similarity	NPC96405
0.7489	Intermediate Similarity	NPC171409
0.7489	Intermediate Similarity	NPC54066
0.7489	Intermediate Similarity	NPC234318
0.7479	Intermediate Similarity	NPC277351
0.7479	Intermediate Similarity	NPC15406
0.7478	Intermediate Similarity	NPC100079
0.7478	Intermediate Similarity	NPC23614
0.7477	Intermediate Similarity	NPC61350
0.746	Intermediate Similarity	NPC100734
0.746	Intermediate Similarity	NPC315634
0.746	Intermediate Similarity	NPC88923
0.7456	Intermediate Similarity	NPC271215
0.7456	Intermediate Similarity	NPC149471
0.7439	Intermediate Similarity	NPC77878
0.7439	Intermediate Similarity	NPC302807
0.7439	Intermediate Similarity	NPC183537
0.7425	Intermediate Similarity	NPC280272
0.7407	Intermediate Similarity	NPC212237
0.7407	Intermediate Similarity	NPC116465
0.7406	Intermediate Similarity	NPC473184
0.7389	Intermediate Similarity	NPC470931
0.7387	Intermediate Similarity	NPC477019
0.7385	Intermediate Similarity	NPC133140
0.7385	Intermediate Similarity	NPC141915
0.7385	Intermediate Similarity	NPC280964
0.7385	Intermediate Similarity	NPC195268
0.7385	Intermediate Similarity	NPC114335
0.7371	Intermediate Similarity	NPC46451
0.7349	Intermediate Similarity	NPC30779
0.7348	Intermediate Similarity	NPC235076
0.7339	Intermediate Similarity	NPC469439
0.733	Intermediate Similarity	NPC224928
0.7328	Intermediate Similarity	NPC134637
0.7325	Intermediate Similarity	NPC188420
0.7325	Intermediate Similarity	NPC119134
0.732	Intermediate Similarity	NPC472589
0.7302	Intermediate Similarity	NPC286119
0.7301	Intermediate Similarity	NPC472111
0.7294	Intermediate Similarity	NPC22115
0.7294	Intermediate Similarity	NPC275680
0.7281	Intermediate Similarity	NPC249996
0.7273	Intermediate Similarity	NPC24260
0.7273	Intermediate Similarity	NPC79293
0.7273	Intermediate Similarity	NPC279401
0.7269	Intermediate Similarity	NPC239824
0.7269	Intermediate Similarity	NPC104196
0.7269	Intermediate Similarity	NPC229373
0.7269	Intermediate Similarity	NPC185639
0.7269	Intermediate Similarity	NPC49075
0.7269	Intermediate Similarity	NPC42663
0.7269	Intermediate Similarity	NPC279228
0.7269	Intermediate Similarity	NPC258657
0.7269	Intermediate Similarity	NPC251735
0.7269	Intermediate Similarity	NPC290582
0.7269	Intermediate Similarity	NPC223690
0.7269	Intermediate Similarity	NPC54654
0.7269	Intermediate Similarity	NPC271013
0.7269	Intermediate Similarity	NPC290005
0.7269	Intermediate Similarity	NPC476202
0.7269	Intermediate Similarity	NPC8836
0.7269	Intermediate Similarity	NPC285931
0.7269	Intermediate Similarity	NPC222661
0.7269	Intermediate Similarity	NPC7715
0.7269	Intermediate Similarity	NPC90998
0.7269	Intermediate Similarity	NPC311973
0.7269	Intermediate Similarity	NPC181796
0.7269	Intermediate Similarity	NPC328155
0.7269	Intermediate Similarity	NPC217748
0.7269	Intermediate Similarity	NPC15414
0.7269	Intermediate Similarity	NPC182052
0.7261	Intermediate Similarity	NPC251160
0.724	Intermediate Similarity	NPC472588
0.7236	Intermediate Similarity	NPC124313
0.7235	Intermediate Similarity	NPC274716
0.7235	Intermediate Similarity	NPC167116
0.7235	Intermediate Similarity	NPC254441
0.7232	Intermediate Similarity	NPC234197
0.7232	Intermediate Similarity	NPC475654
0.7231	Intermediate Similarity	NPC295228
0.7229	Intermediate Similarity	NPC266931
0.7222	Intermediate Similarity	NPC195538
0.722	Intermediate Similarity	NPC473182
0.7209	Intermediate Similarity	NPC101312
0.7209	Intermediate Similarity	NPC473639
0.7205	Intermediate Similarity	NPC215837
0.7205	Intermediate Similarity	NPC469589
0.7202	Intermediate Similarity	NPC95426
0.7202	Intermediate Similarity	NPC16357
0.7202	Intermediate Similarity	NPC302245
0.719	Intermediate Similarity	NPC90875
0.7184	Intermediate Similarity	NPC210296
0.7182	Intermediate Similarity	NPC206900
0.7181	Intermediate Similarity	NPC210256
0.7178	Intermediate Similarity	NPC233334
0.7169	Intermediate Similarity	NPC139783
0.7169	Intermediate Similarity	NPC65312
0.7162	Intermediate Similarity	NPC30182
0.7162	Intermediate Similarity	NPC478092
0.7162	Intermediate Similarity	NPC478091
0.7162	Intermediate Similarity	NPC473589
0.716	Intermediate Similarity	NPC67401
0.7155	Intermediate Similarity	NPC473185
0.7154	Intermediate Similarity	NPC84164
0.7154	Intermediate Similarity	NPC207283
0.715	Intermediate Similarity	NPC152680
0.715	Intermediate Similarity	NPC190783
0.715	Intermediate Similarity	NPC232386
0.7149	Intermediate Similarity	NPC329631
0.7143	Intermediate Similarity	NPC473449
0.7137	Intermediate Similarity	NPC246658
0.713	Intermediate Similarity	NPC473053
0.7126	Intermediate Similarity	NPC160100
0.7119	Intermediate Similarity	NPC132642
0.7117	Intermediate Similarity	NPC478093
0.7114	Intermediate Similarity	NPC99891
0.7113	Intermediate Similarity	NPC214980
0.7104	Intermediate Similarity	NPC274661
0.7104	Intermediate Similarity	NPC175890
0.7104	Intermediate Similarity	NPC82457
0.7104	Intermediate Similarity	NPC48490
0.7104	Intermediate Similarity	NPC11296
0.7093	Intermediate Similarity	NPC199277
0.7093	Intermediate Similarity	NPC135887
0.7083	Intermediate Similarity	NPC293093
0.708	Intermediate Similarity	NPC11017
0.7072	Intermediate Similarity	NPC191132
0.7072	Intermediate Similarity	NPC60295
0.7066	Intermediate Similarity	NPC475253
0.7056	Intermediate Similarity	NPC312872
0.7054	Intermediate Similarity	NPC252251
0.7052	Intermediate Similarity	NPC203373
0.7043	Intermediate Similarity	NPC209981
0.704	Intermediate Similarity	NPC78284
0.7034	Intermediate Similarity	NPC173080
0.7034	Intermediate Similarity	NPC469594
0.7028	Intermediate Similarity	NPC472434
0.7028	Intermediate Similarity	NPC24465
0.7027	Intermediate Similarity	NPC470042
0.7025	Intermediate Similarity	NPC24019
0.702	Intermediate Similarity	NPC108342
0.7017	Intermediate Similarity	NPC121069
0.7014	Intermediate Similarity	NPC14507
0.7014	Intermediate Similarity	NPC47077
0.7014	Intermediate Similarity	NPC477186
0.7014	Intermediate Similarity	NPC320088

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC476995 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	221
0.1-0.2	650
0.2-0.3	996
0.3-0.4	1712
0.4-0.5	2674
0.5-0.6	2204
0.6-0.7	646
0.7-0.8	47
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7982	Intermediate Similarity	NPD7222	Phase 2
0.795	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD7417	Discontinued
0.7738	Intermediate Similarity	NPD7452	Approved
0.7738	Intermediate Similarity	NPD7453	Approved
0.7714	Intermediate Similarity	NPD7169	Suspended
0.766	Intermediate Similarity	NPD6494	Phase 2
0.7644	Intermediate Similarity	NPD3815	Phase 1
0.7644	Intermediate Similarity	NPD3816	Phase 1
0.7639	Intermediate Similarity	NPD4418	Discontinued
0.7611	Intermediate Similarity	NPD7955	Approved
0.7611	Intermediate Similarity	NPD7956	Approved
0.7581	Intermediate Similarity	NPD7708	Approved
0.757	Intermediate Similarity	NPD6773	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD7862	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD7803	Approved
0.7424	Intermediate Similarity	NPD5903	Approved
0.7424	Intermediate Similarity	NPD5902	Approved
0.7422	Intermediate Similarity	NPD5429	Discontinued
0.7403	Intermediate Similarity	NPD7395	Discontinued
0.7398	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD3922	Approved
0.7385	Intermediate Similarity	NPD3924	Approved
0.7385	Intermediate Similarity	NPD3923	Approved
0.7385	Intermediate Similarity	NPD3921	Approved
0.7371	Intermediate Similarity	NPD3763	Approved
0.7366	Intermediate Similarity	NPD1483	Discontinued
0.7364	Intermediate Similarity	NPD6550	Discontinued
0.7358	Intermediate Similarity	NPD3920	Phase 2
0.7355	Intermediate Similarity	NPD7025	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD7859	Phase 2
0.7336	Intermediate Similarity	NPD7069	Discontinued
0.73	Intermediate Similarity	NPD6553	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD6716	Phase 1
0.7292	Intermediate Similarity	NPD7558	Phase 2
0.7269	Intermediate Similarity	NPD8054	Approved
0.7269	Intermediate Similarity	NPD8053	Approved
0.7269	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD5512	Phase 3
0.7175	Intermediate Similarity	NPD6988	Phase 1
0.7168	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD5612	Discontinued
0.7155	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD6569	Phase 2
0.7143	Intermediate Similarity	NPD4502	Phase 2
0.712	Intermediate Similarity	NPD8101	Phase 3
0.7098	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD7682	Approved
0.7088	Intermediate Similarity	NPD7684	Approved
0.7087	Intermediate Similarity	NPD5658	Approved
0.7085	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD5530	Phase 1
0.7071	Intermediate Similarity	NPD7719	Discontinued
0.7051	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7046	Intermediate Similarity	NPD7180	Phase 3
0.7042	Intermediate Similarity	NPD7676	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD7675	Phase 3
0.7042	Intermediate Similarity	NPD7674	Phase 3
0.704	Intermediate Similarity	NPD7868	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5866	Approved
0.7034	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD4889	Approved
0.7031	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD8052	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7004	Intermediate Similarity	NPD7886	Phase 2
0.7004	Intermediate Similarity	NPD7194	Discontinued
0.7004	Intermediate Similarity	NPD7885	Phase 2
0.7	Intermediate Similarity	NPD8100	Phase 3
0.7	Intermediate Similarity	NPD4305	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5256	Discontinued
0.7	Intermediate Similarity	NPD3003	Approved
0.6991	Remote Similarity	NPD8156	Discontinued
0.698	Remote Similarity	NPD6963	Approved
0.698	Remote Similarity	NPD6964	Approved
0.6972	Remote Similarity	NPD4204	Approved
0.6972	Remote Similarity	NPD4203	Approved
0.6971	Remote Similarity	NPD7426	Phase 1
0.6971	Remote Similarity	NPD3263	Phase 3
0.6968	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD7796	Approved
0.6967	Remote Similarity	NPD7797	Approved
0.6964	Remote Similarity	NPD6361	Phase 2
0.6962	Remote Similarity	NPD6985	Discontinued
0.696	Remote Similarity	NPD3837	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4038	Approved
0.6957	Remote Similarity	NPD4035	Approved
0.6957	Remote Similarity	NPD4037	Approved
0.6957	Remote Similarity	NPD4033	Approved
0.6957	Remote Similarity	NPD32	Approved
0.6957	Remote Similarity	NPD4039	Approved
0.6957	Remote Similarity	NPD31	Approved
0.6957	Remote Similarity	NPD4034	Approved
0.6957	Remote Similarity	NPD4036	Approved
0.6957	Remote Similarity	NPD4122	Approved
0.6946	Remote Similarity	NPD5506	Approved
0.6946	Remote Similarity	NPD5507	Approved
0.6944	Remote Similarity	NPD8251	Approved
0.6944	Remote Similarity	NPD8099	Discontinued
0.6944	Remote Similarity	NPD8252	Approved
0.6937	Remote Similarity	NPD7906	Approved
0.6933	Remote Similarity	NPD6590	Discontinued
0.6933	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6974	Phase 3
0.6932	Remote Similarity	NPD8359	Phase 2
0.693	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6926	Remote Similarity	NPD3842	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD6140	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD5930	Phase 3
0.6904	Remote Similarity	NPD7678	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD8463	Approved
0.6898	Remote Similarity	NPD4885	Approved
0.6897	Remote Similarity	NPD7673	Phase 3
0.6895	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8442	Discontinued
0.6872	Remote Similarity	NPD7994	Phase 2
0.687	Remote Similarity	NPD4080	Discontinued
0.6867	Remote Similarity	NPD8016	Phase 3
0.6867	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD5945	Phase 1
0.6864	Remote Similarity	NPD5944	Phase 1
0.6862	Remote Similarity	NPD3875	Discontinued
0.6857	Remote Similarity	NPD6962	Phase 2
0.6851	Remote Similarity	NPD4131	Phase 3
0.685	Remote Similarity	NPD5482	Discontinued
0.6849	Remote Similarity	NPD5164	Discontinued
0.6848	Remote Similarity	NPD8244	Phase 2
0.6844	Remote Similarity	NPD8364	Approved
0.6844	Remote Similarity	NPD8363	Approved
0.6835	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD4897	Phase 2
0.6833	Remote Similarity	NPD5070	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD8091	Phase 3
0.682	Remote Similarity	NPD6568	Discontinued
0.6816	Remote Similarity	NPD8467	Approved
0.6816	Remote Similarity	NPD8465	Approved
0.6816	Remote Similarity	NPD8466	Approved
0.6815	Remote Similarity	NPD4454	Phase 2
0.6813	Remote Similarity	NPD6517	Phase 3
0.6802	Remote Similarity	NPD4373	Phase 2
0.6795	Remote Similarity	NPD7672	Approved
0.6795	Remote Similarity	NPD5863	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD7671	Approved
0.6792	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6787	Remote Similarity	NPD7549	Discontinued
0.6787	Remote Similarity	NPD5805	Approved
0.678	Remote Similarity	NPD6220	Phase 3
0.678	Remote Similarity	NPD5416	Discontinued
0.6774	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.676	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD6159	Phase 2
0.6754	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD3477	Phase 2
0.6752	Remote Similarity	NPD7263	Phase 2
0.6752	Remote Similarity	NPD6290	Phase 2
0.675	Remote Similarity	NPD5632	Approved
0.6745	Remote Similarity	NPD8102	Discontinued
0.6744	Remote Similarity	NPD5677	Discontinued
0.6742	Remote Similarity	NPD3386	Phase 2
0.674	Remote Similarity	NPD4551	Phase 2
0.6739	Remote Similarity	NPD1768	Approved
0.6736	Remote Similarity	NPD5147	Discontinued
0.6735	Remote Similarity	NPD6327	Phase 1
0.6735	Remote Similarity	NPD6326	Phase 2
0.6732	Remote Similarity	NPD5488	Discontinued
0.6719	Remote Similarity	NPD8152	Approved
0.6719	Remote Similarity	NPD8153	Approved
0.6716	Remote Similarity	NPD8459	Approved
0.6716	Remote Similarity	NPD8425	Approved
0.6716	Remote Similarity	NPD8460	Approved
0.6716	Remote Similarity	NPD8426	Approved
0.6709	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD3328	Phase 2
0.6696	Remote Similarity	NPD7777	Approved
0.6696	Remote Similarity	NPD7778	Approved
0.6696	Remote Similarity	NPD53	Approved
0.6691	Remote Similarity	NPD8428	Approved
0.6691	Remote Similarity	NPD8429	Approved
0.6691	Remote Similarity	NPD8427	Approved
0.6682	Remote Similarity	NPD4675	Approved
0.6682	Remote Similarity	NPD4678	Approved
0.6682	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD4927	Discontinued
0.6681	Remote Similarity	NPD5582	Discontinued
0.668	Remote Similarity	NPD4875	Phase 3
0.668	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.668	Remote Similarity	NPD7022	Phase 2
0.668	Remote Similarity	NPD4876	Phase 3
0.668	Remote Similarity	NPD7853	Phase 2
0.668	Remote Similarity	NPD4952	Phase 3
0.668	Remote Similarity	NPD7567	Approved
0.6679	Remote Similarity	NPD7690	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data